Who Do You Call on a S**t Tuesday?

In partnership with

Hey there -

Early in my business, I figured out fast that I didn't want to operate in a vacuum.

I missed having colleagues. I missed being able to turn around and ask someone a question. And as a new business owner, I was hitting firsts constantly, with no idea what the right move was.

So I created a list.

It was a handful of coaches and other solopreneurs who were further down the road than me. They were people I felt comfortable calling when I had no clue what to do next.

That's the whole story. There was no strategy behind it. I just needed people to call.

What I didn't understand at the time was that I had built the most valuable professional asset I own during a stretch when things were “fine.”  That timing turned out to be my saving grace.

Because when the shit hit the fan, and I felt completely out of my depth, I had support.

I wished more leaders followed suit. Over and over, I see the same repeating pattern: Life happens, and they can't (or won't) ask for help, so they hunker down and work harder. Which inevitably means their quality of life and their relationships take the hit. Lather, rinse, and repeat. 

And then they pick their head up one day, and can’t figure out why they’re so exhausted. 

When I ask who they lean on for support, they say some version of "I haven't really gotten into it with anyone."

That isn't because they don't have a network, mind you. These are senior people with hundreds of connections. They (mostly) have a network. 

What they don't have is a short list of people they can call on a random Tuesday when it's all going to hell in a handbasket to say "I have no idea what to do here." 

Leadership is lonely. (Duh.)

The higher you go, the number of people you can share vulnerably and honestly with begins to shrink. (Double duh.) Which is exactly the time when the problems get gnarlier.

🔥Make your list now, so it's in place when you need it. 🔥

You only need 4-5 people. Here's a recommended lineup:

1. Someone one or two steps ahead of you. You want someone close enough to your situation that they still remember what it’s like and far enough ahead that they can offer some perspective. 

2. Someone who will tell you you're wrong. If everyone on your board makes you feel better, you don't have a board. You have a fan club, and fan clubs are terrible at strategy.

3. Someone from outside your industry. This is the person likely to ask a seemingly obvious question that turns out to be the game changer. 

4. Someone who knows you well. Probably someone who knew you before you stepped into the big title.  They will remind you of who you are, what you’ve overcome in the past, and what you stand for. This is useful information to have access to when you've temporarily lost the thread.

5. Someone whose job is to focus on you. That might be a coach (ahem 👋🏼), a therapist, mentor, or an advisor. It's the one relationship where you don't have to reciprocate, don't have to ‘make a good impression’, or wonder whether you're taking up too much space.

Building the list is the easy part, whereas asking often feels like an imposition.

It's neither. Think about the last time someone came to you for advice. Were you annoyed? Or were you a little flattered, and glad they thought of you?

That's your answer. You already know how this works. You've just decided it doesn't apply to you.

We live in a relationship economy. Work gets done with and through other people, and we need to stop pretending otherwise. 

The people who navigate the hard stretches well aren't tougher than everyone else. They just made the calls earlier. 

So who's on your list? And if the answer is nobody, who gets the first call?

Have a great week! 

S

Reply to everything. Edit nothing.

Your inbox is full. Slack is piling up. Client messages need a response yesterday. Typing thoughtful replies to all of it takes hours you don't have.

Wispr Flow turns your voice into clean, professional text you can send the moment you stop talking. Speak like you would to a colleague — tangents and all — and get polished output. Emails, Slack, LinkedIn, WhatsApp, whatever's open.

89% of messages sent with zero edits. Used by teams at OpenAI, Vercel, and Clay. Works on Mac, Windows, and iPhone.

Try Wispr Flow free

WORK WITH ME

If you're a senior leader who looks composed on the outside but feels like you're running version 1.0 of yourself in a version 2.0 role, we should talk.

Executive Coaching - For senior leaders who've earned the role but don't feel solid in it. The gap is costing you. Let's close it.

Corporate Leadership Development - Custom programs for your organization. Not off-the-shelf. Designed around what your people need.

Keynote Speaking - I speak to senior leadership teams about the foundation that makes everything else work: knowing yourself at a deeper level to lead at the next one.

If any of this sounds familiar, let's talk. [email protected] | 617-306-6037